172479-51-5Relevant articles and documents
In situ generation of N -Boc-protected alkenyl imines: Controlling the e / Z geometry of alkenyl moieties in the Mukaiyama-Mannich reaction
Bai, Jian-Fei,Sasagawa, Hajime,Yurino, Taiga,Kano, Taichi,Maruoka, Keiji
, p. 8203 - 8206 (2017/07/24)
Readily available Boc-protected Z-alkenyl aminals could be used as Z-alkenyl and E-alkenyl imine precursors under acidic conditions. In the Mukaiyama-Mannich reaction of Z-alkenyl Boc-aminals, the E/Z geometry of the products was controlled by the catalys
Highly Functionalized Organolithium Reagents for Enantiomerically Pure α-Amino Acid Synthesis
Kenworthy, Martin N.,Kilburn, John Paul,Taylor, Richard J. K.
, p. 19 - 22 (2007/10/03)
(Equation presented) Highly functionalized L-serine-derived organolithium reagents have been generated and reacted with a variety of electrophiles, delivering novel enantiomerically pure adducts. These adducts were then converted into homochiral amino alcohols and novel nonproteinogenic α-amino acids, including an aspartic acid mimic that has been synthesized in an enantiomerically pure form for the first time.
Carbonylative coupling of organozinc reagents in the presence and absence of aryl iodides: Synthesis of unsymmetrical and symmetrical ketones
Jackson, Richard F. W.,Turner, Debra,Block, Michael H.
, p. 865 - 870 (2007/10/03)
The utility of the palladium(o) catalysed reaction of the iodoalanine-derived organozinc reagent 6a with functionalised aryl iodides, under a carbon monoxide atmosphere, to give protected 4-aryl-4-oxo α-amino acids 8, is illustrated by a short synthesis of L-kynurenine 4. Treatment of functionalised organozinc reagents with catalytic tetrakis(triphenylphosphine)palladium(0) under an atmosphere of carbon monoxide in the absence of any electrophile leads to the formation of symmetrical functionalised ketones 9 in good yields. This reaction is illustrated by a one-step synthesis of protected (2S,6S)-4-oxo-2,6-diaminopimelic acid 9a from commercially available compounds. It has been established that adventitious molecular oxygen plays a key role in the formation of the symmetrical ketones 9, and that rigorous exclusion of oxygen can result in substantially higher yields of ketones 8 in the cross-coupling with some aromatic iodides.
